(S)-(+)-3-(Benzyloxycarbonyl)-5-oxo-4-oxazolidinepropionic acid → (S)-5-oxo-3-[(phenylmethoxy)carbonyl]-4-Oxazolidinepropanal

HRID 52256Notes

Reaction equation

HRID 52256 reaction equation
[O:1]=[C:2]1[O:6][CH2:5][N:4]([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[C@H:3]1[CH2:17][CH2:18][C:19](O)=[O:20].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>C1COCC1.C(Cl)Cl>[O:1]=[C:2]1[O:6][CH2:5][N:4]([C:7]([O:9][CH2:10][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)=[O:8])[C@H:3]1[CH2:17][CH2:18][CH:19]=[O:20]

Participants

5

Reactant 2

HCID 688249(S)-(+)-3-(Benzyloxycarbonyl)-5-oxo-4-oxazolidinepropionic acidHCID 178418287HCID 178418287, compound

Product 1

HCID 11022192(S)-5-oxo-3-[(phenylmethoxy)carbonyl]-4-OxazolidinepropanalYield 51.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 27 g (92.7 mmol) of the crude acid (43c) in 200 mL of THF is cooled to 0° C. and 13 mL (10.7 g, 141 mmol) of borane-methyl sulfide complex is added dropwise via an addition funnel. The reaction is allowed to warm gradually to room temperature and stirred for 12 h. The resulting mixture is concentrated in vacuo to give a white glassy material which is taken up in 500 mL of methylene chloride and treated with of pyridinium chlorochromate (61 g, 281 mmol) at 0° C. in the presence of 3 -- molecular sieve. The mixture is allowed to warm to room temperature and stirred for 3 h. The mixture is filtered through diatomaceous earth with ether (200 mL) then concentrated. The residue is taken up in ether and filtered again through diatomaceous earth with ether then concentrated to give 13.22 g of the crude aldehyde as a light green oil: NMR δ9.80 (br s, 1H), 7.40 (m, 5H), 5.55 (br s, 1H), 5.20 (m, 3H), 4.38 (t, J=6.0 Hz, 1H), 2.6-2.1 (m, 4H).

Workup

  1. addition13 mL (10.7 g, 141 mmol) of borane-methyl sulfide complex is added dropwise via an addition funnel
  2. concentrationThe resulting mixture is concentrated in vacuo
  3. customto give a white glassy material which
  4. temperatureto warm to room temperature
  5. stirringstirred for 3 h
  6. filtrationThe mixture is filtered through diatomaceous earth with ether (200 mL)
  7. concentrationthen concentrated
  8. filtrationfiltered again through diatomaceous earth with ether
  9. concentrationthen concentrated

Sources & evidence

ORD record
ord-cb6b50b1b2cd4def96255639be5cae24
Source dataset
uspto-grants-1997_04
Patent number
US05616612

Reaction notes

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